I bought about $7000 worth of Bitcoin and Ethereum in July as an experiment and learning process. Well, it is now worth about $21,000.

I had planned to buy and hold until July 2018 so any gains would be long-term, but the recent run-up has me worrying the bubble pop may come sooner. I can afford to lose the initial investment (I kind of expected to), but would rather not .

I have long-term capital losses that could offset $3000 of gains both in 2017 and 2018. I am in the highest marginal income tax bracket for short-term gains.

As I see it, I have a few options.

1. Sell it all in 2017. Incur $14,000 in gains and offset $3000.
2. Sell half in 2017, half in January 2018. Incur $14,000 gains and offset $6000.
3. Ride the rollercoaster until July 2018 and sell then.

Someone magically drops 14,000 in your lap, BUT there's a catch! The catch is you have to pay a 44% tax (39.6%+3.8%+0.9%) if you want to keep most of it. Bird in hand is better than two in a bush. Pay the toll and exit right.

Someone magically drops 14,000 in your lap, BUT there's a catch! The catch is you have to pay a 44% tax (39.6%+3.8%+0.9%) if you want to keep most of it. Bird in hand is better than two in a bush. Pay the toll and exit right.

Yep dropped the gift limit into a 529 and maxed a HSA with some to spare. Called it a happy day.

Let it all ride since the loss will not have consequences. Missing out on a significant gain may make you have regrets for a long time. Even though it may be a bubble, it may go on for years to come (or maybe not).

I'm risk adverse. I'd sell $7000 now to recoup my initial money. Now I'm even (and have my emotions under control). Then I'd simply start taking out any future gains on the remainder on a weekly basis. Once it dropped a predetermined amount (just for giggles and grins lets say I decided 10%) I'd sell the remainder. If it continues to go up, I win. If it starts to drop I cash out - and I win.

i would suggest. selling some immediately to cover your 7k.. then in the new year... i'd sell more to get down to 7k in bitcoin.

at this point you would have covered your "experiment" and got that money back. Taken a profit.. And still retain the amount of bitcoin you where willing to do an experiment with.

Then periodically, i'd check in on that remaining bitcoin, and if appropriate (loaded word)... i'd continue to take profits to reduce my risk back towards that 7k figure i was willing to go to Las Vegas with.

Depending on things we don't know, your "play" money may actually be causing more stress than fun.

Interesting concept. And may not apply to you at all, but I'm sure it applies to somebody somewhere.

An idea - sell half now and pay the high tax and be happy you made money. Keep the other half and see if it makes it to long term cap gains. Then you'll know for sure which was the better decision that you got half the benefit of. Seems like a win-win to me.

I bought about $7000 worth of Bitcoin and Ethereum in July as an experiment and learning process. Well, it is now worth about $21,000.

I had planned to buy and hold until July 2018 so any gains would be long-term, but the recent run-up has me worrying the bubble pop may come sooner. I can afford to lose the initial investment (I kind of expected to), but would rather not .

I have long-term capital losses that could offset $3000 of gains both in 2017 and 2018. I am in the highest marginal income tax bracket for short-term gains.

As I see it, I have a few options.

1. Sell it all in 2017. Incur $14,000 in gains and offset $3000.
2. Sell half in 2017, half in January 2018. Incur $14,000 gains and offset $6000.
3. Ride the rollercoaster until July 2018 and sell then.

Any soothsayers out there? What would you do in my situation?

Thanks,
cc

Why not reverse dollar-cost average out of Bitcoin? Sell $4.5k this month, and an equal amount every following month until you are out of Bitcoin.

"Everything should be as simple as it is, but not simpler." - Albert Einstein |
Wiki article link:Getting Started

1. Sell it all in 2017. Incur $14,000 in gains and offset $3000.
2. Sell half in 2017, half in January 2018. Incur $14,000 gains and offset $6000.
3. Ride the rollercoaster until July 2018 and sell then.

Something doesn't seem right here. I think you could sell it all today and use the entire $6k. I think the $3k limit each year is against ordinary income, not agains capital gains. However, I don't do any of this and could be wrong.

I'm in nearly the exact same boat. I bought mine last March as basically a lottery ticket (using a tiny percentage of my portfolio that I was perfectly willing to risk). My thought being that I'd hate to have missed out on the "opportunity of a lifetime" when the entry point was fairly modest. What I hadn't counted on was all of this near term upside. I really had no exit strategy.

I now feel like I'm on "Let's make a deal". I can cash out now for a really nice gain or I can choose door #2.

I really like the idea of taking ongoing periodic withdrawals in order to hold the line at the original spend. Maybe I'll start that next week...or the week after.

I bought about $7000 worth of Bitcoin and Ethereum in July as an experiment and learning process. Well, it is now worth about $21,000.

I had planned to buy and hold until July 2018 so any gains would be long-term, but the recent run-up has me worrying the bubble pop may come sooner. I can afford to lose the initial investment (I kind of expected to), but would rather not .

I have long-term capital losses that could offset $3000 of gains both in 2017 and 2018. I am in the highest marginal income tax bracket for short-term gains.

As I see it, I have a few options.

1. Sell it all in 2017. Incur $14,000 in gains and offset $3000.
2. Sell half in 2017, half in January 2018. Incur $14,000 gains and offset $6000.
3. Ride the rollercoaster until July 2018 and sell then.

Any soothsayers out there? What would you do in my situation?

Thanks,
cc

Based on my own dot com experience (my employer's stock went way high, dropped in half, I did not sell, eventually sold for maybe 10% of peak).

I would sell half right now. You have not made money at the casino until you have taken some off the table.

The rest you can ride until July of next year.

Until you have taken some out you have not made any money on this. Half a pie is better than no pie (and the whole pie is not twice as happy as half a pie).

I bought about $7000 worth of Bitcoin and Ethereum in July as an experiment and learning process. Well, it is now worth about $21,000.

I had planned to buy and hold until July 2018 so any gains would be long-term, but the recent run-up has me worrying the bubble pop may come sooner. I can afford to lose the initial investment (I kind of expected to), but would rather not .

I have long-term capital losses that could offset $3000 of gains both in 2017 and 2018. I am in the highest marginal income tax bracket for short-term gains.

As I see it, I have a few options.

1. Sell it all in 2017. Incur $14,000 in gains and offset $3000.
2. Sell half in 2017, half in January 2018. Incur $14,000 gains and offset $6000.
3. Ride the rollercoaster until July 2018 and sell then.

Any soothsayers out there? What would you do in my situation?

Thanks,
cc

Since your investment tripled, you are in the catbird seat. At this point, you should take action so that no matter what happens you will feel like a winner.

If you sell nothing and it crashes you will lose everything including your initial $7,000.
If you sell everything and it continues up, you will be have 3x, but no more participation if it goes up 10x.
If you sell $7,000 and it crashes you will have no gain or loss.
If you sell $14,000 you have locked in a 2x gain. and still have a chance for more gains.

IMO it's more like gambling on getting into a pyramid scheme and getting back out before it collapses. You'd probably need a crystal ball to make even a wild guess about how it might do in the future either up or down. It has NO intrinsic value that can be used to evaluate it, so it all depends on what the next speculator will be willing to pay.

One day last week it dropped over 20% in 90 minutes. It has dropped as much as about 57% in a single day, and something like 75% in the worst 3 and 6 months periods. Not my kind of investment.

But not to worry. I seem to remember reading that John Bogle thinks it will level out at maybe $100 someday, but according to Portfolio Visualizer so far it has never lost more than about 83% of its value, and that took 5 months (From July to November 2011). That time it only took 1 year 7 months to recover.

The second worst drop was only about 79.8% (in 1 year 9 months from Dec 2013 to Aug 2015). Then it took 3 years 3 months to recover.

I suspect that if you had it in a pile of cash and set it on fire, you'd probably need to soak it in gasoline first and fan the flame to make sure it would lose as much as it has done by itself in a single day.

Here are some gee-whiz number showing the worst days. This is daily data from yahoo.

My wife almost talked me into getting a bitcoin about a year ago when it popped up on NPR and I was investigating it because it sounded cool. I am pretty sure I would've sold it after a 25 percent gain and called myself lucky. I'd be wacky if I had kept it.

We just talked about it a few minutes ago. I was like, "You know 'Fear of missing out''? I don't have that. I don't regret not buying it, because if I had kept it, I'd be watching the price nonstop. Where's the value in that?"

Nope I fully exited when the price hit $7k and wont go back now that it's in the secondary market (less miners more purchasers) and the sorry state of cryptocurrency encryption code or lack there of.

Don't even get me started on the wallet code, hopefully you have yours in a offline hard drive wallet.

Happened to my son and his friend who mined in the early days (09, 10) when it was easy and quick with a slow machine to fill up the wallet. Then they lost the wallet (or password or whatever). Could have paid for college. Oh well.

Not a soothsayer, but, like you, I am holding a small position in crypto (BTC, ETH, LTC and BTG). Looking at it today and something in me is screaming "sell", but I don't think I can (lol..). I kind of feel like a member of the Titanic's band, but I kind of think I'll just ride it out a bit and see where it goes. I thought about taking the original investment off the table and leaving the gains, but, as you point out, it's not a lot of money in the grand scheme of things and if the upside is something ridiculous then I'll really be kicking myself for pulling the original out. Then again, if it goes to zero I'll really be kicking myself for not pulling it out. Thank goodness almost everything else is in index funds.

Not a soothsayer, but, like you, I am holding a small position in crypto (BTC, ETH, LTC and BTG). Looking at it today and something in me is screaming "sell", but I don't think I can (lol..). I kind of feel like a member of the Titanic's band, but I kind of think I'll just ride it out a bit and see where it goes. I thought about taking the original investment off the table and leaving the gains, but, as you point out, it's not a lot of money in the grand scheme of things and if the upside is something ridiculous then I'll really be kicking myself for pulling the original out. Then again, if it goes to zero I'll really be kicking myself for not pulling it out. Thank goodness almost everything else is in index funds.

Good luck!

OP here.

I would kick myself more if I don't sell and it goes to zero than if I do sell and it continues to rise. I have convinced myself with the comments here that it's time to cash in and walk away. It was a worthwhile exercise for sure.

Not a soothsayer, but, like you, I am holding a small position in crypto (BTC, ETH, LTC and BTG). Looking at it today and something in me is screaming "sell", but I don't think I can (lol..). I kind of feel like a member of the Titanic's band, but I kind of think I'll just ride it out a bit and see where it goes. I thought about taking the original investment off the table and leaving the gains, but, as you point out, it's not a lot of money in the grand scheme of things and if the upside is something ridiculous then I'll really be kicking myself for pulling the original out. Then again, if it goes to zero I'll really be kicking myself for not pulling it out. Thank goodness almost everything else is in index funds.

Good luck!

OP here.

I would kick myself more if I don't sell and it goes to zero than if I do sell and it continues to rise. I have convinced myself with the comments here that it's time to cash in and walk away. It was a worthwhile exercise for sure.

Not a soothsayer, but, like you, I am holding a small position in crypto (BTC, ETH, LTC and BTG). Looking at it today and something in me is screaming "sell", but I don't think I can (lol..). I kind of feel like a member of the Titanic's band, but I kind of think I'll just ride it out a bit and see where it goes. I thought about taking the original investment off the table and leaving the gains, but, as you point out, it's not a lot of money in the grand scheme of things and if the upside is something ridiculous then I'll really be kicking myself for pulling the original out. Then again, if it goes to zero I'll really be kicking myself for not pulling it out. Thank goodness almost everything else is in index funds.

Good luck!

OP here.

I would kick myself more if I don't sell and it goes to zero than if I do sell and it continues to rise. I have convinced myself with the comments here that it's time to cash in and walk away. It was a worthwhile exercise for sure.

Thanks,
cc

I bought some btc yesterday. Glad to be the next sucker to support your exit! Thank you for your post as a reminder that having a strategy ahead of time makes the sell decisions easier. FWIW my btc is 0.3% of my "investments".

Last edited by lolbatross on Wed Dec 06, 2017 8:55 am, edited 1 time in total.

This kind of thing can be a lot of fun. My guess is it is near the end of a bubble cycle since suddenly everyone I know is talking about it and thinking about "investing". It is amazing watching people do the mental gymnastics to justify getting in. In my experience, once you get that last big push from all the copycats who hear about it on the morning news it is usually the best time to bail.

“Should I sell this gimmick and guarantee a ridiculous return on investment or should I be greedy and risk losing once the inevitable bubble bursts?”

Tough decision

lol...yeah, when you put it like that.. I think I'll give it a few days and see what the CBOE futures do to the price. I may move some off my Trezor and into an online wallet/exchange so I can be ready to pull the plug.

Remember the stock CMGI? You don't have gains and actual $$ until you sell. I don't know what the future holds but with large gains and a questionable future, don't ride this into the ground. FWIW, I would be selling large junks of it. I learned from my past mistakes. Good luck.